(2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid

• ChemBase ID: 3058
• Molecular Formular: C9H9I2NO3
• Molecular Mass: 432.9816
• Monoisotopic Mass: 432.86718915
• SMILES: N[C@@H](Cc1cc(c(c(c1)I)O)I)C(=O)O
• Canonical SMILES: OC(=O)[C@H](Cc1cc(I)c(c(c1)I)O)N
• InChI: InChI=1S/C9H9I2NO3/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,13H,3,12H2,(H,14,15)/t7-/m0/s1
• InChIKey: NYPYHUZRZVSYKL-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid
• IUPAC Traditional name: DL-3,5-diiodotyrosine; 3,5-diiodotyrosine
• Synonyms: 3,5-Diiodotyrosine; Diiodotyrosine; 3,5-Diiodo-L-tyrosine dihydrate; 3,5-Diiodo-4-Hydroxy-β-Phenylalanine; 3,5-DIIODO-L-TYROSINE; 3,5-Diiodo-4-Hydroxy-beta-Phenylalanine

Database IDs

• CAS Number: 300-39-0; 66-02-4; 18835-59-1
• EC Number: 206-092-0
• MDL Number: MFCD00016542; MFCD00150275
• Beilstein Number: 2218691
• PubChem SID: 160966504; 24893289; 46507686; 24863801
• PubChem CID: 9305; 6181
• Chemspider ID: 8946
• MeSH Name: Diiodotyrosine
• Unique Ingredient Identifier: 6L57Q44ZWW
• Wikipedia Title: Diiodotyrosine

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.48031414
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.36174458
• LogD (pH = 7.4): -0.01126826
• Log P: 0.3690121
• Molar Refractivity: 73.8222 cm^3
• Polarizability: 29.323618 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.7
• LOG S: -2.92
• Solubility (Water): 5.19e-01 g/l

PROPERTIES

Physical Property

• Apperance: white crystalline
• Melting Point: 199-201 °C (dec.); 200 °C (dec.)(lit.); 213°C
• Optical Rotation: [α]/D +1.2±0.4°, c = 5% in 1 M HCl; [α]20/D +1.2±0.4°, c = 5% in 1 M HCl; [α]20/D +1.5°, c = 4 in 1 M HCl

Safety Information

• Storage Condition: 0°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98.0% (NT); 95+%; 98%
• Empirical Formula (Hill Notation): C9H9I2NO3 · 2H2O
• Classification: Rare Genuine Natural Compounds

DETAILS

MP Biomedicals - 05205032

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150914

White crystals

DrugBank - DB03374

• Drug Groups: experimental
• Description: A product from the iodination of MONOIODOTYROSINE. In the biosynthesis of thyroid hormones, diiodotyrosine residues are coupled with other monoiodotyrosine or diiodotyrosine residues to form T4 or T3 thyroid hormones (THYROXINE and TRIIODOTHYRONINE). [PubChem]

Sigma Aldrich - 51783

Application
Intermediate in the biosynthesis and alternative pathways of metabolism1 of thyroid hormones. Substrate for the assay of halogenated tyrosine and thyroid hormone aminotransferase2,3

Sigma Aldrich - D0754

Application
Substrate for the assay of halogenated tyrosine and thyroid hormone aminotransferase.1,2 Intermediate in the biosynthesis and alternative pathways of metabolism of thyroid hormones.3

Sigma Aldrich - 38130

Other Notes
Intermediate in the biosynthesis and alternative pathways of metabolism1 of thyroid hormones. Substrate for the assay of halogenated tyrosine and thyroid hormone aminotransferase2,3